Where oh where do I start? Portland is near and dear to my heart. I have been living here on and off for the last five years and it has such a charm. It is home of the weird. Home of the beer, the food, the homeless, the liberal artists, the wall art graffiti, and the strip clubs. You can dress however you want, be whoever you please, and pretty much get away with it without weird looks. One weekend in Portland is hardly enough time to explore this lovely city, but I will try!

The first thing to know when planning your trip, is that Portland is kind of like a big little city. If you come here for a weekend, or a long weekend, it is practically impossible to see everything, especially without a car. If you end up coming for just one weekend, the best thing to do is stick within your neighborhood or rent a car if you have the flexibility. Furthermore, sure, we have great public transit, and it can take you to different parts of the city, but then you are going to be wasting time in transit when you could be eating, drinking, and shopping more! within your own area!

Sadly, one important thing to note is the homeless population has gone up tremendously over the last few years. It is not unusual to see homeless tents on people’s property, tent camps in parking lots, or aggressive homeless people. Unfortunately, you do need to be careful when walking in downtown and the outside neighborhoods seem to be a little “safer.”

Moreover, when planning your trip to Portland it is good to know that the city is ‘divided’ into different sections (in my eyes). You have NE/N, SE, SW (pretty much downtown), NW, and downtown. Therefore, each neighborhood will have a different vibe, and I guarantee you will fall in love with each location. One weekend in Portland is hardly enough to see it all, but you could try to see 1-2 of the neighborhoods. Some things to note is that many places unfortunately closed down after COVID so you will want to double check that these places are still open OR if they need reservations! Below I will write a quick sentence about each neighborhood and my favorite drink and eating spots.

NE/N:
Looking for the art scene and hipster scene with rad concerts and shows? Then NE/N is for you!
Gravy for breakfast
Pine State Biscuits for breakfast
City State Diner for breakfast/brunch
Matador for happy hour
Steeplejack for drinks and to check out the AMAZING UNIQUE interior
Culmination Brewing for beer
Great Notion Brewing for AMAZING sour IPAS!
Breakside Brewery for beer
McMenamins Kennedy School for soaking pool (reserve), drinks and food!
Migration Brewing Company for beer
Por Que No for margaritas and food or walking anywhere on Mississippi Ave!

SE:
Looking for thrift shops, the cutest neighborhoods, accessibility to multiple different SE streets by foot, unique bars and restaurants & city parks? Then one weekend in Portland adventuring SE is for you!
Now, SE is my favorite location and where I currently live so it’s incredibly hard for me to just pick a few but I will try!
The Hazel Room for breakfast/brunch
Bread & Ink Cafe for breakfast
Farmhouse Kitchen for amazing thai food
Bellwether Bar for great cocktails and limited food menu
Vintage for wonderful cocktails
Aalto Lounge for food and cocktails
Pied Coffee House for outdoor hookah, cool vibes, and minimal food menu
Bamboo Sushi for food
Kens Artisan Pizza for food
Apizza Scholls for food
Cubo for empanadas, checking out the ambiance, and drinks
Bible Club for drinks and ambiance
Revolution Hall for it’s rooftop view
Rimsky-Korsakoffee House for its coffee and dessert

SW:
To be honest many people don’t actually stay here when they are visiting for the weekend as it is more residential based, so I won’t get into it- or parts of it are considered “downtown” so I will list restaurants and bars in the downtown section below

NW:
Looking for upscale boutiques, restaurants and bars, accessibility to city hiking trails (forest park), and the San Francisco vibe? Then one weekend in Portland adventuring NW is for you!
Matador
Brix Tavern
10 Barrell Brewing
Back Pedal Brewing Company
Deschutes Brewery (super tasty food and drinks!)
Can Font for Spanish Tapas or Bar Casa Vale
Papa Haydn for dessert you will keep coming back for
Besaws for cocktails
Escape from New York Pizza for a slice of heavenly pizza

Downtown:
Looking for a hodgepodge of vibes, killer views, walkability, accessibility with public transit, and not afraid of seeing some homeless? Then one weekend in Portland adventuring downtown is for you!
Mothers Bistro Bar for breakfast/brunch
Kingsland Kitchen for breakfast/brunch
Hubers Cafe for thanksgiving food year-round and a flaming (what a show!) Spanish tequila coffee
Departure for late night happy hour, views, cocktails and food
Portland City Grill for late night happy hour, views, cocktails and food
1927 S’mores Company for the best hot chocolate and s’mores

I know the above are definitely overwhelming, but at least you can google those places to see how close/far they are from where you end up staying and go from there!

Finally, IF you have rented a car my suggested weekend itinerary would be:
Friday night: settle in to your hotel and air b& b, then get dinner and drinks!
Saturday: Get ready for an ALL day adventure. Have snacks available, comfortable shoes, a rain jacket (you never know), and water!
General Itinerary: Breakfast, drive the Columbia River Gorge, Lunch, OHSU Tram, Council Crest Park and other views, Dinner & Drinks at Departure, Hot chocolate and smores
Breakfast: Your choice! There are so many options so choose what is close to you.
Columbia River Gorge: Drive out to the Vista House and then Multnomah Falls. Along the way from Vista to the Falls, you will see a plethora of other waterfalls to stop at such as Latourell and Wahkeena… definitely do them all! This should take approximately 2-3 hours to sight see all the falls.
Lunch at Sugarpine Drive-In: On you way back and close to Multnomah Falls, you will find the cutest drive in. The menu is on the more limited side, but their “waffle” grilled cheese sandwich, tomato soup and soft serve is to die for! Not to mention the cuteness of this entire walk up stand, it’s definitely a must visit!
After having a yummy lunch, go and check out the stellar views while taking the tram (pretty much like a giant covered gondola) from the waterfront to the Oregon Health and Science University hospital. Yes, I know you think I’m crazy, go to a hospital? Seriously though. If you park at the waterfront, you can experience the amazing view us hospital staff get to see every day. Stay here for a bit and take in the views!
As you make your way back down with the tram, take your car and drive to these scenic, must see spots: Council Crest Park, Pittock Mansion, and the Washington Park International Rose Test Garden. I know this sounds like a lot and pretty overwhelming, but each spot is 5-10 minutes from each other and shouldn’t take more than 5-10 minutes soaking in the views, so try to go to all of them if you can! After you have made it to all these places, you have earned a drink and dinner!
Dinner and drinks at Departure or Portland City Grill. These restaurants by far have some of the best views!
Finally, the end of the night, you have eaten dinner, had a yummy cocktail, and now you just want to go home and relax. First, head to 1927 S’mores Company which is just a few minutes away from the downtown location where you just had dinner. Here, you will go into a chocolate coma and be ready for bed in no time!

Sunday: Sleep in and relax! Check out the local farmers markets, walk Mount Tabor or explore the Pearl District on foot. Before you get too far into your day, head over to Korsacoffee If you end up going to the Pearl District, you will want to check out the world’s largest independent bookstore, Powell’s Books. You may get hungry and head over to Escape from New York Pizza for some amazing, sliced pizza or Matador for kick a** happy hour nachos!

It’s a bit of a walk but along the way you can then walk along NW 23rd, stopping frequently for drinks and snacks. You can then end the night at the rooftop bar, Revolution Hall, or grab a coffee and dessert at Rimsky-Korsakoffee House. To end the night, you can get some more Portland vibes by smoking hookah outdoors at Pied Cow Coffeehouse. Beware that this place does close at 10 PM so you will want to get there a little earlier to experience the ambience.

Also, who knows, maybe you will want to rent a bike and just bike all along the waterfront!

Monday: Finally, as this is the day you will be flying out, spend the day in your neighborhood, wherever you chose to stay… you can’t go wrong!

Finally, I hope you enjoyed the one weekend itinerary of Portland!

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